1. Field of the Invention
This invention relates to new chemical compounds of value as antibacterial agents. More particularly it relates to monoesters and diesters of certain 1,1-alkanediol dicarboxylates in which a penicillin carboxyl group and/or the carboxyl group of certain beta-lactamase inhibitors are esterified.
2. Description of the Prior Art
Penicillanic acid 1,1-dioxide (sulbactam) is known from U.S. Pat. No. 4,234,579 to be an effective beta-lactamase inhibitor and antibacterial agent.
In U.S. Pat. No. 4,244,951 bis-esters of formula (IX) are disclosed in which sulbactam is coupled to known antibacterial penicillins via methanediol. ##STR3## In the above formula R.sub.1 represents certain acyl groups of known antibacterial penicillins. For example, R.sub.1 can represent 2-amino-2-phenylacetyl or 2-amino-2-(p-hydroxyphenyl)acetyl.
In U.S. Pat. No. 4,342,772 issued Aug. 3, 1982, analogous compounds are disclosed in which penicillins and beta-lactamase inhibitors such as penicillanic acid 1,1-dioxide, clavulanic acid and 6-beta-halopenicillanic acids are linked via 1,1-alkanediol groups.
In copending application Ser. No. 300,421, filed Sept. 9, 1981, now abandoned, and assigned to the same assignee, compounds of formula (IX) are disclosed wherein R.sub.1 is ##STR4## and R.sub.2 is certain alkyl or alkoxy groups.
Ampicillin, 6-[D-(2-amino-2-phenylacetamido)]-penicillanic acid is disclosed in U.S. Pat. No. 2,985,648. Amoxicillin, 6-[D-(2-amino-2-[p-hydroxyphenyl]acetamide)]penicillanic acid is known from U.S. Pat. No. 3,192,198 and U.S. Pat. No. Re. 28,744. p-Acyl derivatives of amoxicillin are disclosed in U.S. Pat. Nos. 2,985,648, 3,520,876 and 4,053,360.
2-beta-Acetoxymethyl-2-alpha-methyl-penam-3-alpha-carboxylic acid 1,1-dioxide is disclosed as being a useful beta-lactamase inhibitor in U.S. Pat. No. 4,256,733.
2-beta-Chloromethyl-2-alpha-methyl-penam-3-alpha-carboxylic acid 1,1-dioxide is disclosed as a beta-lactamase inhibitor in British Patent Application No. 2,070,592.
Bis-Esters of 1,1-alkanediols with 6-beta-hydroxymethylpenicillanic acid 1,1-dioxide are disclosed in U.S. Pat. No. 4,342,768. The corresponding derivatives of 6-alpha-hydroxymethylpenicillanic acid 1,1-dioxide are disclosed in copending application Ser. No. 338,794, filed Jan. 11, 1982, assigned to the same assignee. 6-Aminoalkyl penicillanic acid 1,1-dioxide beta-lactamase inhibitors are disclosed in copending application Ser. No. 388,324, filed June 14, 1982 now abandoned and assigned to the same assignee.